Jaye by Christie Brown ****** I'm writing this letter because the other day I was talking with a friend and the subject of wearing high heels for extended periods of time came up. When I started wearing heels, I stopped wearing anything else, except when I had to wear boy clothes. I started as soon as I graduated from highschool and left my parents house. In my first jobs I couldn't dress but whenever I was home I wore heels all the time. Virtually all the pairs I purchased were 4"-5". I found myself always looking forward to the weekend when I could spend 48 hrs. in my heels. Friday after work the second I got home I would start primping, laying out my outfits for the weekend, doing my make-up, putting on my lingerie. When I was done I felt so sexy and hot. One of the best things though was the simple pleasure of actually being able to reach the highest shelves in my kitchen. Around 10:00 I usually would go out dancing. I love to show off my legs in a short skirt and dancing is a great way to do it. Out on the dance floor I felt so wonderful. I can be such a tease I love dancing close to my partner running my nails across the bulge in his crotch. At first I was too scared to bring someone home to my apartment so usually I would do some heavy petting in the back of a guys car, finishing him by swallowing his delicious cum. Once in a while, usually when I'd had to many drinks I would have a guy fuck me standing up, out back of the bar in an alley or parking lot. I still think it's one of the best ways to please a man. Even today now and then I'll pick a guy up in a bar just so I can get him to fuck me in the alley outback. I get so turned on thinking about a guys hands up my skirt holding my cheeks wide. My anus already lubed with K-Y for his pleasure and ease of penetration when he enters my supple ass with his manly, hard dick. My back against the brick wall of an alley legs wrapped around his. With each thrust I can hear my coat rubbing against the brick wall. I even have a few decent pictures of these scenes my coat open in front draped around my legs, long thin heels with a pointy toe pointed toward the sky, a look of ecstasy on my face. These pictures are a great way to start a masturbation session with my vibrator. On my best nights I can get 3 hot dicks up my ass, in-between dancing with all the horny guys. By the time I get home my panties are wet and sticky from all the cum that's leaked out of my exquisitely sore boy pussy. About a year after I started my job at an insurance agency I was offered the chance to work at home filling in claims forms on a computer. It's a great job because I almost never have to go into the office. So virtually everyday I can dress in tight sexy outfits. The ability to dress as a sex starved boy/girl everyday really improved my skills at passing. One problem it created though was after about a year it became difficult to flatten my foot comfortably, even sneakers became uncomfortable so I had to wear heels all the time. Of course this meant I had to more or less live full time as a woman. Its a thrill to go to QFC fully dressed. All the guys think I'm a very sexy, slutty woman. There used to be this really cute box boy that I would give a show to. Bending over to get something from a low shelf, instead of bending my knees and lowering myself in a lady like manner I would bend from the waist. I could feel my short skirt sliding against my stockings and garters as it hiked itself up my ass. I always wore an especially short skirt for these shows, it was easy to see my garters and panties when I was bent over. After I stood up I'd make a small production of pulling my skirt down, leaving just a bit of my upper stockings showing. The look on the kids face was fabulous. After about 3 years I couldn't wear anything lower than 4" or it would really hurt. When I try anything lower than 4", my calves start to really hurt almost immediately and they stay sore for the next few days during which I have to wear 5" heels till the pain goes away. The only time I wear flats is the few days each month when I have to go into the office. The pain of wearing flats is hell. When I started I never really thought of living full time as a woman, I'm not a transsexual I'm just a bisexual male who prefers to look like a pretty if somewhat mannish appearing woman. You would never call my facial features cute, but when I've done a good job with my make-up I think I look sexy. I have shoes called mules, that I wear at night sometimes and in the shower. I can walk on my toes if I have to, but my calves get tired fast so its easier to wear a pair of Frederick's of Hollywood Mules. Mules are heels, like pumps, but with nothing covering the heel of the foot, so they slip on like slippers. I don't sleep in them often but with the partners I usually pick up, they often ask me to. So I have many times. The nice thing about having a high heel fetish is the number of men that share the fetish. Bisexual males like me who love looking and acting like woman are not the most popular partners in the gay world. But when I walk into a hot bar in a short skin tight dress and 5" heels I never have any trouble finding some companionship for the night. Its a great feeling, I love sitting on a barstool my legs crossed demurely and having a nice strong man flirt with me, touching my thigh, running his fingers along the outline of my garters. I figure that as long as I put out the only guys worth talking to are ones will buy me drinks, call me a whore if you want but it seems fair to me.. I have about 20 pair of 4" and higher heels, and about 5 or 6 pair of boots with 4"-5" heels. Most of them are black, because black goes with everything. I have about every color though! I have 4 or 5 pair that are 5 1/2" I think. My foot is already somewhat hyperextended when I wear those though. I only wear a size 7, so 5" heels are quite high already. I find 4 1/2" to be the most comfortable. The return of 70's fashions has been a thrill, platform heels are so sexy. I just recently bought a pair with 6" heels and a 1" platform, I can wear these with no problem because as far as my foot is concerned they are effectively 5" heels. I look so fuckably hot in these with a tight pair of Levis and a black bodysuit. In the winter I wear my boots mostly, a couple only come up to the knee, but the rest reach mid thigh. I get really turned on looking in the mirror and seeing my self in thigh high boots that end a few inches below my skirt. One of my favorite outfits is a sheer blouse over a satin padded push-up bra, no panties, and thigh high boots under a shiny black trenchcoat. I'm so easily accessible when dressed this way, I've even managed to get a nice stiff dick up my ass while still sitting at the bar. The guy I was dancing with took me over to the bar and found a stool for me to rest on, but the bar was so crowded he had to stand behind me. While I was sitting there I ordered up a couple of shots of Tequila. When the juice hit me I was feeling really good. But all the sudden I felt his hands rubbing my ass. He had slipped them through the split in the back of my coat. He was whispering in my ear, telling me he was gonna fuck me right here. For some dam reason on this particular night I hadn't lubed my ass before I left home, so at first I was thinking this was a bad idea. But when I felt one of his hands let go and heard his zipper, I decided I better get ready and scooted back on the stool far enough that the rear of my ass was hanging off the back. I was amazed that no one could tell what was going on. When I felt his dick start squeezing its way into my anus without the help of any KY I let out the slightest yelp of pain. To help ease the pain as he sliding all the way home I downed another shot. Between the Tequila, the feeling of doing something so sleazy and the pain, it was the best sex I've ever had without being tied up first. A couple nights later when I stopped by the bar. I found out quite a few people had noticed what was going on. Ever since then when I go in wearing a trenchcoat the bartender always makes sure I have a stool to sit on. One problem I have now after having been wearing heels for so long is that its difficult to go to the beach or a park in the summer. I don't go that often but when I do, I have to wear a pair of pumps. Another problem I have is my body, when I'm fully dressed I just look like a very well toned young woman ( And I should. I work out a couple of hours every morning, in heels no less.), but when I am in a revealing bathing suit my muscles and the flatness of my chest make me look like a female body builder or very fem guy. I started wearing heels because I like how they look and what they do for the appearance of my legs. The first time I tried walking in them I realized that if I really wanted to get used to them, so that they wouldn't bother me when I wore them for extended periods. I would have to wear them a lot. I figured that if I just wore them as much as possible, I would get used to them and they would feel normal. I was right but sometimes its tough never being able to go barefoot comfortably. Now that I'm 26 and 5''10" in my heels (that was another reason I started wearing them and wanted to get used to them. In stalking feet and garters I'm only 5'5"). I can't imagine living any other way. FIN .